|“|| Elena: Who is that?|
Damon: This.. is Lillian Salvatore.
Elena: Your mother is alive?
Damon: Yep. Turns out she's been in a Prison World, snapshot of 1903, for over a century.
— Damon telling Elena about his mother's status
DAMON TRAVELS TO THE 1903 PRISON WORLD - With the help of Bonnie and Kai, Damon and Elena set forth a plan to rescue Damon’s mother, Lily, who is trapped in the 1903 prison world. Meanwhile, when Caroline's plan for Stefan backfires, she is left to pick up the pieces. Elsewhere, back at Whitmore College, Enzo and Alaric’s attempt to reel Caroline back in doesn’t quite go as planned when they realize they're outmaneuvered. Lastly, an unexpected gift from Bonnie leaves Damon shaken to his core.
- Antagonists: Stefan and Caroline
- The episode title refers to Stefan and Damon's mother, Lily Salvatore, and the Prison World that she's in.
- This is the third time this season that Elena and Damon have worked together since Damon's return from the 1994 Prison World.
- This is the first episode to feature two vampires, Stefan and Caroline, with their humanity turned off.
- This episode is the second episode to feature spring break at Whitmore College. The first was While You Were Sleeping.
- Enzo and Alaric meet for the first time on-screen in this episode. They had been in contact at the beginning of the season when looking for a lead to Damon's whereabouts, but hadn't shared a scene until this point.
- Stefan makes Caroline's life miserable by 'teaching' her how to exact proper revenge when your humanity is off, so that she will let go of her carefully controlled life and enjoy herself fully instead. Eventually, after resisting him all day, she gives in when he uses her desire to feed on human blood against her.
- Stefan and Caroline have sex for the first time.
- With this episode, Elena and Caroline have both had sex with the same three men in the series. Similarly, those three men, Matt, Stefan and Damon, have also all had sex with the same three female characters: Elena, Rebekah and Caroline.
- Lily tells Elena and Damon how she became a vampire in 1858 at the TB ward after she was fed vampire blood by a nurse, which caused her to wake up in transition after she died from the disease. She also explained that the reason she left her sons in her husband's care instead of taking them with her was to protect them from her uncontrolled bloodlust.
- Based on the date given by Lily for her imprisonment on the night of October 31, 1903, this means she was placed in the prison world one month before the Wright brothers flight at Kittyhawk, NC.
- Damon greets his mother Lily in the same manner in which he greeted Stefan in the Pilot, with "Hello, Mother" instead of saying brother.
- Damon tells Elena that his mother will only be a means to bring back Stefan's humanity, nothing more and Elena agrees with him. However she also believes there might be some good in Lily and that it will take time for him to see it.
- It's revealed that in 1903 that the same house that Stefan and Damon grew up in is still standing.
- Elena invites herself on the trip to the 1903 Prison World to meet Lily, stating that she wants to see the woman who gave birth to the two epic loves of her life. While there she finds a picture of Stefan as child at first mistaking it for one of Damon until Damon shows her a picture of himself as a child with Lily. She then takes the photo with her, as she says there are no baby pictures of her boyfriend.
- Lily claims to only drink two drops of animal blood a week, due to the low blood supply in the Prison World.
- Lily Salvatore leaves the 1903 Prison World and Bonnie and Damon arrange for Kai to be left behind.
- Bonnie, while in 1994 getting Silas's headstone, discovers that the cure still existed in the prison world. She gives it to Damon so that he can decide what to do with it. When he suggests that he doesn't want to give it to Elena anymore, Bonnie tells him that it's up to him how the cure is used, and he can give it to Elena or to someone else.
- Bonnie's mother, Abby, is mentioned in this episode. When Bonnie gives the cure to Damon, she tells him that she had planned to give it to her mother but she was "surprisingly happy" as a vampire.
- The cure would also exist in the 1903 Prison World as well, the same as Silas' tombstone infused with Qetsiyah's blood and magic. Kai like, Bonnie can make use of Silas' Tombstone to free himself and Lily's vampire "family."
- Jo agrees to hold Sarah for a day until Elena's blood is out her system so she doesn't become another Salvatore vampire, as they too are aware that Sarah Nelson is a Salvatore.
- Enzo gives up on his plan to get revenge on Stefan, having grown disillusioned with it after Alaric told him that it was only a way to deal with his loneliness. He then tells Sarah the truth about who he is and apparently tells her about her parentage.
- This is the first of two episodes to feature all four currently living members of the Salvatore family: Stefan, Damon, Lily and Sarah.
- Female Student - Drained of blood; killed by Stefan Salvatore and Caroline Forbes.
- Director - Decapitation; killed by Stefan Salvatore
- Jo, Lily and Alaric were last seen in Let Her Go.
- Giuseppe Salvatore was mentioned in this episode by Lily and Damon. He was last seen in Handle with Care as a flash of Stefan's memories.
- Going by the rules of the show, the college girl should be transitioning if she dies since she has Caroline's blood in her system.
- Abby Bennett Wilson was mentioned by Bonnie. She was last seen in Season Four's A View to a Kill.
- McKinley, Virginia
Behind the Scenes
- This episode had about 1.59 million viewers in the USA.
- Hashtag during the airing is #MamaSalvatore
- "A Bird in a Gilded Cage" is a song composed by Arthur J. Lamb (lyrics) and Harry Von Tilzer (music). It was a sentimental ballad (or tear-jerker) that became one of the most popular songs of 1900.
- This title marks a shift from naming each episode this season after songs released in 1994, to songs from the early 20th century, which is consistent with a transition from the 1994 prison world to the 1903 prison world.
- "It's the Hard-Knock Life" is a song from the musical Annie with music by Charles Strouse and lyrics by Martin Charnin, which was used in the song "Hard Knock Life" by Jay-Z. Enzo quotes it while talking to Caroline.
- "The Gilded Age" is a period of US history from the late 19th century, about 1870s to about the year 1900, to the early 20th century.